Tetrahedron p. 3689 - 3696 (1986)
Update date:2022-07-29
Topics:
Bergman, Jan
Brynolf, Anna
Vuorinen, Eino
Addition of Grignard or organolithium reagents to N-(α-haloacyl)-N-alkylsubstituted anthranilonitriles (e.g.N-(2-bromopropionyl)-N-methyl-2-cyanoaniline)induced anion formation followed by cyclization to 4-amino-2-quinolinones (e.g. 4-amino-1,3-dimethyl-2-quinolinone (10)).Substrates lacking α-hydrogen atoms, such as N-α-bromoisobutyryl)-2-cyanoaniline, also yielded 3,3-dimethylquinolinedione (9b) by cyclization.In these cases the initial step is a halogen-metal exchange reaction.
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